Acetic Acid → HCID 68312821, compound

HRID 1472922Notes

Reaction equation

HRID 1472922 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[N:14]=[C:13]([CH:15]=O)[CH:12]=[CH:11][CH:10]=2)[CH:5]=[CH:6][C:7]=1[F:8].[NH2:17][C:18]1([CH2:23][OH:24])[CH2:22][CH2:21][CH2:20][CH2:19]1.C(O)(=O)C.C([BH3-])#N>CO.C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[N:14]=[C:13]([CH2:15][NH:17][C:18]3([CH2:23][OH:24])[CH2:22][CH2:21][CH2:20][CH2:19]3)[CH:12]=[CH:11][CH:10]=2)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 663071-AminocyclopentanemethanolHCID 498716Cyano-borohydrideHCID 72942664HCID 72942664, compound

Product 1

HCID 68312821HCID 68312821, compoundYield 59%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of Example 266A (0.500 g, 2.12 mmol) in methanol (20 mL) and CH2Cl2 (20 mL) at ambient temperature was added cycloleucinol (0.244 g, 2.12 mmol), acetic acid (0.50 mL, 8.5 mmol) followed by MP-cyanoborohydride (2.49 mmol/g; 1.0 g). After 2 hours, the mixture was filtered, concentrated and the residue partitioned between ether and 1N NaOH. The organic extract was concentrated and purified by chromatography to provide 418 mg (59%) of the title compound. MS (DCI+) m/z 335 (M+H); 1H NMR (500 MHz, CDCl3) δ 8.03 (dd, J=7.1, 2.2 Hz, 1H), 7.86 (ddd, J=8.6, 4.6, 2.3 Hz, 1H), 7.73 (t, J=7.8 Hz, 1H), 7.55 (d, J=7.8 Hz, 1H), 7.30-7.19 (m, 2H), 3.95 (s, 2H), 3.48 (s, 2H), 1.87-1.52 (m, 8H).

Workup

  1. filtrationthe mixture was filtered
  2. concentrationconcentrated
  3. customthe residue partitioned between ether and 1N NaOH
  4. extractionThe organic extract
  5. concentrationwas concentrated
  6. custompurified by chromatography

Sources & evidence

ORD record
ord-a1595657962a4870b3f0a217f6293405
Source dataset
uspto-grants-2015_04
Patent number
US09012651B2

Reaction notes

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